Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /All experiences
    3. /Sailing

    Best results for Sailing

    Showing 337-360 of 497 results
    Key West Full-Day Private Sailing Charter
    Key West, FL

    Key West Full-Day Private Sailing Charter

    Sail, snorkel, and explore Key West waters on your private catamaran

    Sail, snorkel, and explore Key West waters on your private catamaran
    4.8 • 71 reviews
    $2,452& up
    Key West Full-Day Sail & Snorkel Charter
    Key West, FL

    Key West Full-Day Sail & Snorkel Charter

    Customize a private day on the water with snorkeling and onboard lunch

    Customize a private day on the water with snorkeling and onboard lunch
    4.8 • 19 reviews
    $1,060
    Miami Yacht Party Cruise
    Miami, FL

    Miami Yacht Party Cruise

    Swim, socialize, and sightsee on a sailing yacht in Biscayne Bay

    Swim, socialize, and sightsee on a sailing yacht in Biscayne Bay
    4.0 • 166 reviews
    $149/ person
    Hobie Wave Sailing Rental in Key Biscayne
    Key Biscayne, FL

    Hobie Wave Sailing Rental in Key Biscayne

    Sail Biscayne Bay on a stable Hobie Wave catamaran

    Sail Biscayne Bay on a stable Hobie Wave catamaran
    $113/ boat
    Key Biscayne 1-Hour Hobie Getaway Sailboat Rental
    Key Biscayne, FL

    Key Biscayne 1-Hour Hobie Getaway Sailboat Rental

    Cruise and swim aboard a stable Hobie Getaway catamaran

    Cruise and swim aboard a stable Hobie Getaway catamaran
    $170/ boat
    Biscayne Bay Eco Sailing Tour
    Miami, FL

    Biscayne Bay Eco Sailing Tour

    Sail Biscayne Bay’s sandbars and mangroves while looking for local wildlife

    Sail Biscayne Bay’s sandbars and mangroves while looking for local wildlife
    $159/ person
    Miami 40' Sailing Catamaran Charter
    Miami, FL

    Miami 40' Sailing Catamaran Charter

    Sail aboard a 40-foot catamaran with giant nets and an interior cabin

    Sail aboard a 40-foot catamaran with giant nets and an interior cabin
    4.0 • 166 reviews
    $456/ hour
    1-Hour Windsurfing Lesson in Key Biscayne
    Key Biscayne, FL

    1-Hour Windsurfing Lesson in Key Biscayne

    Build windsurfing fundamentals in calm, shallow water

    Build windsurfing fundamentals in calm, shallow water
    $85
    Miami Sunset Cruise
    Miami, FL

    Miami Sunset Cruise

    Champagne toast and sunset views on Biscayne Bay

    Champagne toast and sunset views on Biscayne Bay
    4.0 • 166 reviews
    $86/ person
    Fort Myers Beach Day Sail
    Fort Myers Beach, FL

    Fort Myers Beach Day Sail

    Sail Fort Myers Beach waters with opportunities to spot local marine life

    Sail Fort Myers Beach waters with opportunities to spot local marine life
    5.0 • 567 reviews
    $68/ person
    8-Hour Private Charter to Upper Captiva
    Fort Myers Beach, FL

    8-Hour Private Charter to Upper Captiva

    Sail to secluded Upper Captiva beaches for shelling, swimming, and relaxation

    Sail to secluded Upper Captiva beaches for shelling, swimming, and relaxation
    5.0 • 567 reviews
    $2,475
    Fort Myers Beach Sunset Sailing Charter
    Fort Myers Beach, FL

    Fort Myers Beach Sunset Sailing Charter

    Watch the Gulf sunset from your own private boat

    Watch the Gulf sunset from your own private boat
    5.0 • 567 reviews
    $1,350
    Naples 2-Hour Sailing Charter
    Naples, FL

    Naples 2-Hour Sailing Charter

    Private catamaran sailing around the Ten Thousands Islands

    Private catamaran sailing around the Ten Thousands Islands
    $336
    Naples 4-Hour Sailing Charter
    Naples, FL

    Naples 4-Hour Sailing Charter

    Sail to barrier islands on a private morning or afternoon outing

    Sail to barrier islands on a private morning or afternoon outing
    $672
    Private Sailing Charter in Hilton Head Island
    Hilton Head Island, SC

    Private Sailing Charter in Hilton Head Island

    Set sail on a private charter with room for your own food and drinks

    Set sail on a private charter with room for your own food and drinks
    4.9 • 51 reviews
    $996& up
    Private Sunset Sail in Hilton Head Island
    Hilton Head Island, SC

    Private Sunset Sail in Hilton Head Island

    An evening sailing charter with space for your own food and drinks

    An evening sailing charter with space for your own food and drinks
    4.9 • 51 reviews
    $1,550& up
    2-Hour Sailing Cruise in Hilton Head Island
    Hilton Head Island, SC

    2-Hour Sailing Cruise in Hilton Head Island

    Enjoy a daytime sail and time on the water

    Enjoy a daytime sail and time on the water
    4.9 • 51 reviews
    $55/ person
    Hilton Head Sunset Dolphin Sailing Charter
    Hilton Head, SC

    Hilton Head Sunset Dolphin Sailing Charter

    Sail into sunset with coastal wildlife and ecology insights

    Sail into sunset with coastal wildlife and ecology insights
    4.9 • 116 reviews
    $508
    Hilton Head Island Sunset Sail
    Hilton Head Island, SC

    Hilton Head Island Sunset Sail

    Toast the evening aboard a relaxed coastal catamaran sail

    Toast the evening aboard a relaxed coastal catamaran sail
    4.9 • 51 reviews
    $89/ person
    America's Cup Sailing Cruise in Hilton Head
    Hilton Head Island, SC

    America's Cup Sailing Cruise in Hilton Head

    Sail Hilton Head’s coast aboard the historic Stars & Stripes

    Sail Hilton Head’s coast aboard the historic Stars & Stripes
    4.8 • 7.9K reviews
    $1,204
    Brunch Sailing Cruise in Hilton Head Island
    Hilton Head Island, SC

    Brunch Sailing Cruise in Hilton Head Island

    Savor brunch and drinks aboard a Lowcountry catamaran

    Savor brunch and drinks aboard a Lowcountry catamaran
    4.9 • 51 reviews
    $105/ person
    Hilton Head Island Sunset Cruise
    Hilton Head Island, SC

    Hilton Head Island Sunset Cruise

    Sail into sunset with room for your group and your own refreshments

    Sail into sunset with room for your group and your own refreshments
    4.9 • 51 reviews
    $1,328& up
    Dolphin Watch Sail in Hilton Head Island
    Bluffton, SC

    Dolphin Watch Sail in Hilton Head Island

    Private wind-powered sailing with hands-on fun

    Private wind-powered sailing with hands-on fun
    $525& up
    Private Morning Sail in Hilton Head
    Bluffton, SC

    Private Morning Sail in Hilton Head

    Sail into a quieter morning on Hilton Head waters

    Sail into a quieter morning on Hilton Head waters
    $504& up
    1…141516…21